Saquinavir mesylate
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MedKoo CAT#: 326756

CAS#: 149845-06-7 (mesylate)

Description: Saquinavir, also known as Ro 31-8959, is an antiretroviral drug used together with other medications to treat or prevent HIV/AIDS. Typically it is used with ritonavir or lopinavir/ritonavir to increase its affect. Saquinavir is a protease inhibitor. Saquinavir binds to the active site of the viral protease and prevents cleavage of viral polyproteins, preventing maturation of the virus. Saquinavir inhibits both HIV-1 and HIV-2 proteases.


Chemical Structure

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Saquinavir mesylate
CAS# 149845-06-7 (mesylate)

Theoretical Analysis

MedKoo Cat#: 326756
Name: Saquinavir mesylate
CAS#: 149845-06-7 (mesylate)
Chemical Formula: C39H54N6O8S
Exact Mass: 0.00
Molecular Weight: 766.960
Elemental Analysis: C, 61.08; H, 7.10; N, 10.96; O, 16.69; S, 4.18

Price and Availability

Size Price Availability Quantity
5mg USD 300 2 Weeks
10mg USD 500 2 Weeks
50mg USD 800 2 Weeks
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Related CAS #: 149845-06-7 (mesylate)   127779-20-8 (free base)    

Synonym: Ro 31-8959; Ro 31-8959/000; Ro 318959; Sch 52852; Sch-52852; Sch52852; Saquinavir; brand names Invirase and Fortovase.

IUPAC/Chemical Name: (S)-N1-((2S,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-phenylbutan-2-yl)-2-(quinoline-2-carboxamido)succinamide mesylate

InChi Key: IRHXGOXEBNJUSN-YOXDLBRISA-N

InChi Code: InChI=1S/C38H50N6O5.CH4O3S/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29;1-5(2,3)4/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49);1H3,(H,2,3,4)/t26-,27+,30-,31-,32-,33+;/m0./s1

SMILES Code: CS(=O)(O)=O.O=C(C1=NC2=C(C=CC=C2)C=C1)N[C@@H](CC(N)=O)C(N[C@@H](CC3=CC=CC=C3)[C@H](O)CN4[C@@H](C[C@@]5([H])[C@@](CCCC5)([H])C4)C(NC(C)(C)C)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Related CAS# CAS#149845-06-7 (Saquinavir mesylate). CAS#127779-20-8 (Saquinavir free base).

Product Data:
Biological target: Saquinavir is an HIV protease inhibitor (Kis = 0.12 and <0.1 nM for HIV-1 and HIV-2 protease, respectively). Saquinavir inhibits replication of clinical isolates of HIV-1 in a variety of cell-based assays and has antiviral activity against HIV-1 in infected C8166 cells (IC50 = 2 nM). It also inhibits the activity of the severe acute respiratory coronavirus 2 (SARS-CoV-2) main protease (Mpro), also known as 3C-like protease (3CLpro), with an IC50 value of 9.92 µM.
In vitro activity: In this study, saquinavir could modulate TLR4-mediated immune responses and consequent risk for uncontrolled inflammation. Saquinavir suppressed both MyD88- and TRIF-dependent pathways in response to LPS, leading to downregulation of NF-κB and IRF3. Saquinavir did not suppress MyD88-dependent pathway triggered by Pam3csk4. Saquinavir did not alleviate IRF3 phosphorylation induced by Poly(I:C). Saquinavir decreased dimerization of TLR4 following LPS or HMGB1 stimulation. Reference: Immunopharmacol Immunotoxicol. 2023 Aug 7:1-7. https://pubmed.ncbi.nlm.nih.gov/37485845/
In vivo activity: Short term saquinavir application improved skull bone healing in a mouse calvarial defect model.Saquinavir may have potential for skeletal repair. It enhanced osteoclast and M2 macrophage infiltration, elevated gene expression related to bone healing, and promoted osteoclastic differentiation. However, high concentrations inhibited cell viability. Reference: Plast Reconstr Surg. 2022 Dec 1;150(6):1264e-1274e. https://pubmed.ncbi.nlm.nih.gov/36112847/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.4 50.00

Preparing Stock Solutions

The following data is based on the product molecular weight 766.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Yao K, Wang Z, Peng C, Wang Y, Xue B, Tang Y, Wang Z, Xu H. HIV protease inhibitor saquinavir inhibits toll-like receptor 4 activation by targeting receptor dimerization. Immunopharmacol Immunotoxicol. 2023 Aug 7:1-7. doi: 10.1080/08923973.2023.2239488. Epub ahead of print. PMID: 37485845. 2. Park S, Auyeung A, Lee DL, Lambert PF, Carchman EH, Sherer NM. HIV-1 Protease Inhibitors Slow HPV16-Driven Cell Proliferation through Targeted Depletion of Viral E6 and E7 Oncoproteins. Cancers (Basel). 2021 Feb 24;13(5):949. doi: 10.3390/cancers13050949. PMID: 33668328; PMCID: PMC7956332. 3. Elgammal Y, Salama EA, Seleem MN. Saquinavir potentiates itraconazole's antifungal activity against multidrug-resistant Candida auris in vitro andin vivo. Med Mycol. 2023 Sep 4;61(9):myad081. doi: 10.1093/mmy/myad081. PMID: 37558393. 4. Liu H, Shen Y, Zhao B, Poon EH, Qi S, Ker DFE, Billiar TR, Cooper GM, Xu Y, Wang D. Short-Term Administration of HIV Protease Inhibitor Saquinavir Improves Skull Bone Healing with Enhanced Osteoclastogenesis. Plast Reconstr Surg. 2022 Dec 1;150(6):1264e-1274e. doi: 10.1097/PRS.0000000000009734. Epub 2022 Sep 19. PMID: 36112847; PMCID: PMC9698106.
In vitro protocol: 1. Yao K, Wang Z, Peng C, Wang Y, Xue B, Tang Y, Wang Z, Xu H. HIV protease inhibitor saquinavir inhibits toll-like receptor 4 activation by targeting receptor dimerization. Immunopharmacol Immunotoxicol. 2023 Aug 7:1-7. doi: 10.1080/08923973.2023.2239488. Epub ahead of print. PMID: 37485845. 2. Park S, Auyeung A, Lee DL, Lambert PF, Carchman EH, Sherer NM. HIV-1 Protease Inhibitors Slow HPV16-Driven Cell Proliferation through Targeted Depletion of Viral E6 and E7 Oncoproteins. Cancers (Basel). 2021 Feb 24;13(5):949. doi: 10.3390/cancers13050949. PMID: 33668328; PMCID: PMC7956332.
In vivo protocol: 1. Elgammal Y, Salama EA, Seleem MN. Saquinavir potentiates itraconazole's antifungal activity against multidrug-resistant Candida auris in vitro andin vivo. Med Mycol. 2023 Sep 4;61(9):myad081. doi: 10.1093/mmy/myad081. PMID: 37558393. 2. Liu H, Shen Y, Zhao B, Poon EH, Qi S, Ker DFE, Billiar TR, Cooper GM, Xu Y, Wang D. Short-Term Administration of HIV Protease Inhibitor Saquinavir Improves Skull Bone Healing with Enhanced Osteoclastogenesis. Plast Reconstr Surg. 2022 Dec 1;150(6):1264e-1274e. doi: 10.1097/PRS.0000000000009734. Epub 2022 Sep 19. PMID: 36112847; PMCID: PMC9698106.

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1: Muret P, Solas C; Groupe Suivi Therapeutique Pharmacologique de la Societe Francaise de Pharmacologie et de Therapeutique. [Evidence-based therapeutic drug monitoring for saquinavir]. Therapie. 2011 May-Jun;66(3):207-12. doi: 10.2515/therapie/2011029. Epub 2011 Aug 9. Review. French. PubMed PMID: 21819804.

2: la Porte CJ. Saquinavir, the pioneer antiretroviral protease inhibitor. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1313-22. doi: 10.1517/17425250903273160. Review. PubMed PMID: 19737048.

3: O'Brien WA 3rd. Saquinavir/Ritonavir: its evolution and current treatment role. AIDS Read. 2006 Jan;16(1):38-44; discussion 43. Review. PubMed PMID: 16433471.

4: Hill A, Walmsley S, Clotet B, Molto J. Analysis of genotypic and phenotypic clinical cut-off levels for ritonavir-boosted saquinavir. HIV Med. 2006 Mar;7(2):67-74. Review. PubMed PMID: 16420251.

5: Johnson M, Peters B. Saquinavir/low-dose ritonavir: its use in HIV infection. AIDS Rev. 2003 Jan-Mar;5(1):44-51. Review. PubMed PMID: 12875107.

6: Plosker GL, Scott LJ. Saquinavir: a review of its use in boosted regimens for treating HIV infection. Drugs. 2003;63(12):1299-324. Review. PubMed PMID: 12790697.

7: Grub S, Delora P, Lüdin E, Duff F, Fletcher CV, Brundage RC, Kline MW, Calles NR, Schwarzwald H, Jorga K. Pharmacokinetics and pharmacodynamics of saquinavir in pediatric patients with human immunodeficiency virus infection. Clin Pharmacol Ther. 2002 Mar;71(3):122-30. Review. PubMed PMID: 11907486.

8: Léautez S, Billaud E. [Value of saquinavir in antiretroviral treatment of adult HIV-1 infection in 2001]. Presse Med. 2001 Sep 22;30(26):1299-303. Review. French. PubMed PMID: 11603093.

9: Gill J, Feinberg J. Saquinavir soft gelatin capsule: a comparative safety review. Drug Saf. 2001;24(3):223-32. Review. PubMed PMID: 11347724.

10: Kravcik S. Pharmacology and clinical experience with saquinavir. Expert Opin Pharmacother. 2001 Feb;2(2):303-15. Review. PubMed PMID: 11336588.

11: Figgitt DP, Plosker GL. Saquinavir soft-gel capsule: an updated review of its use in the management of HIV infection. Drugs. 2000 Aug;60(2):481-516. Review. PubMed PMID: 10983742.

12: Katlama C. [The new saquinavir formulation SGC (Soft Gel Capsule)]. Presse Med. 1999 Apr 17;28(15):815-8. Review. French. PubMed PMID: 10325942.

13: Roberts NA, Craig JC, Sheldon J. Resistance and cross-resistance with saquinavir and other HIV protease inhibitors: theory and practice. AIDS. 1998 Mar 26;12(5):453-60. Review. PubMed PMID: 9543442.

14: Vella S, Floridia M. Saquinavir. Clinical pharmacology and efficacy. Clin Pharmacokinet. 1998 Mar;34(3):189-201. Review. PubMed PMID: 9533981.

15: Perry CM, Noble S. Saquinavir soft-gel capsule formulation. A review of its use in patients with HIV infection. Drugs. 1998 Mar;55(3):461-86. Review. PubMed PMID: 9530549.

16: Hoetelmans RM, Meenhorst PL, Mulder JW, Burger DM, Koks CH, Beijnen JH. Clinical pharmacology of HIV protease inhibitors: focus on saquinavir, indinavir, and ritonavir. Pharm World Sci. 1997 Aug;19(4):159-75. Review. PubMed PMID: 9297727.

17: Boucher C. Rational approaches to resistance: using saquinavir. AIDS. 1996 Nov;10 Suppl 1:S15-9. Review. PubMed PMID: 8970671.

18: Porche DJ. Saquinavir. J Assoc Nurses AIDS Care. 1996 Jul-Aug;7(4):61-4. Review. PubMed PMID: 8875367.

19: Noble S, Faulds D. Saquinavir. A review of its pharmacology and clinical potential in the management of HIV infection. Drugs. 1996 Jul;52(1):93-112. Review. PubMed PMID: 8799687.

20: Bragman K. Saquinavir: an HIV proteinase inhibitor. Adv Exp Med Biol. 1996;394:305-17. Review. PubMed PMID: 8815695.